Bis-β-cyclodextrinyl- and bis-cellobiosyl-diazacrowns: synthesis and molecular complexation behaviors toward Busulfan anticancer agent and two basic aminoacids

Porwanski, Stanislaw; Dumarçay-Charbonnier, Florence; Menuel, S.; Joly, Jean‐Pierre; Bulach, Véronique; Marsura, Alain

doi:10.1016/j.tet.2009.05.057

Cited by 18 publications

(7 citation statements)

References 12 publications

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“…Asymmetric aza-Henry reaction catalyzed by carbohydrate ureas L1-L15 In two of our publications, the discussions on the reactivity and selectivity of various carbohydrate ureas were described. [29][30][31][32] Continuing this study, we demonstrate the results obtained in the presence of new ligands in the asymmetric aza-Henry reaction (Table 1). The previously obtained results are also included in Table 1, in order to demonstrate the influence of the sugar moiety and the base on the reactivity and selectivity of this reaction.…”

Section: © Author(s)supporting

confidence: 63%

Studies on the influence of saccharide fragment of urea organocatalysts on the yield and enantioselectivity of aza-Henry reaction

Robak¹,

Koselak²,

Zawisza³

et al. 2020

Arkivoc

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Six new bifunctional ureas bearing a carbohydrate ring and an optically active base for the asymmetric aza-Henry reaction of imines with nitromethane has been developed. The influence of the saccharide urea fragment and the base in organocatalysts, both new and previously prepared by our team, on the yield and enantioselectivity of aza-Henry reactions was demonstrated. The aza-Henry reaction products were obtained in 17-98% yield and ee up to 99%. The highly enantioselective reaction course is likely the result of the synergic action of two urea fragments -saccharide and DACH.

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Section: © Author(s)supporting

confidence: 63%

Studies on the influence of saccharide fragment of urea organocatalysts on the yield and enantioselectivity of aza-Henry reaction

Robak¹,

Koselak²,

Zawisza³

et al. 2020

Arkivoc

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“…44) bind efficiently S -arginine ( 81d ), S -lysine ( 81c ) and the anticancer agent busulfan [224]. The Job’s plots indicate 1:1 stoichiometries in all the complexes.…”

Section: Reviewmentioning

confidence: 99%

“…Combinations of a diaza-18-crown-6-ether with α-cyclodextrin- ( 67a , 68 ) and celobiosyl- ( 67b ) residues ( Fig. 44 ) bind efficiently S -arginine ( 81d ), S -lysine ( 81c ) and the anticancer agent busulfan [ 224 ]. The Job’s plots indicate 1:1 stoichiometries in all the complexes.…”

Section: Reviewmentioning

confidence: 99%

Molecular recognition of organic ammonium ions in solution using synthetic receptors

Späth¹,

König²

2010

Beilstein J. Org. Chem.

220

130

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SummaryAmmonium ions are ubiquitous in chemistry and molecular biology. Considerable efforts have been undertaken to develop synthetic receptors for their selective molecular recognition. The type of host compounds for organic ammonium ion binding span a wide range from crown ethers to calixarenes to metal complexes. Typical intermolecular interactions are hydrogen bonds, electrostatic and cation–π interactions, hydrophobic interactions or reversible covalent bond formation. In this review we discuss the different classes of synthetic receptors for organic ammonium ion recognition and illustrate the scope and limitations of each class with selected examples from the recent literature. The molecular recognition of ammonium ions in amino acids is included and the enantioselective binding of chiral ammonium ions by synthetic receptors is also covered. In our conclusion we compare the strengths and weaknesses of the different types of ammonium ion receptors which may help to select the best approach for specific applications.

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“…We had earlier described SCHEME 1 compounds 8b, 11b and 9a-b [6,7]. The similar synthetic strategy was used for β-cellobiosyl ligands 6b-8b, which were obtained in high 73-96% yield starting from hepta-O-acetyl-azido-β-D-cellobiose (2).…”

Section: Synthesismentioning

confidence: 99%

“…Recently, we had described derivatives of saccharides and azacrown ethers as efficient drug receptors (such as busulfan, paracetamol, aspirin) [6,7]. Depending on the size of cavity, we had observed both 1/1 and sandwich complexes.…”

Section: Introductionmentioning

confidence: 99%

Stability of the Complexes of Bis-Saccharide Crown Ethers withp-Toluenesulfonamide

2014

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Bis-β-cyclodextrinyl- and bis-cellobiosyl-diazacrowns: synthesis and molecular complexation behaviors toward Busulfan anticancer agent and two basic aminoacids

Cited by 18 publications

References 12 publications

Studies on the influence of saccharide fragment of urea organocatalysts on the yield and enantioselectivity of aza-Henry reaction

Studies on the influence of saccharide fragment of urea organocatalysts on the yield and enantioselectivity of aza-Henry reaction

Molecular recognition of organic ammonium ions in solution using synthetic receptors

Stability of the Complexes of Bis-Saccharide Crown Ethers withp-Toluenesulfonamide

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